The impacts of information technology on business performance has been a focus of research in recent years. In this regard, contingency models based on the notion of «fit » between the organization’s management of IT, its environment, strategy, and structure seem to show promise. Six perspectives are examined as they pertain to the relationships between the firm’s environmental uncertainty, its strategic orientation, its structure, its strategic management of IT, and its performance, namely moderation, mediation and matching as bivariate approaches to fit, and covariation, profile deviation and gestalts as systems approaches. These relationships are analyzed by means of an empirical study of 110 small enterprises. Results obtained from applying and comparing the six perspectives illustrate their significant differences and confirm the need for conceptual and methodological rigor when applying contingency theory in strategic information technology management research.